


Surprises Come In All Shapes And Sizes (Or; The Dare That Literally Bit Stiles In The Ass)

by agirlnamedtruth



Category: Teen Wolf (TV)
Genre: Anal Sex, Barebacking, Biting, Crossdressing, Crossdressing Stiles Stilinski, Dirty Talk, Established Derek Hale/Stiles Stilinski, Explicit Language, Explicit Sexual Content, Feminization, M/M, Manhandling, Panty Kink, Pet Names, Rimming, Rough Sex, Top Derek Hale/Bottom Stiles Stilinski
Language: English
Status: Completed
Published: 2016-11-29
Updated: 2016-11-29
Packaged: 2018-09-03 03:36:42
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,812
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8694829
Author URL: https://archiveofourown.org/users/agirlnamedtruth/pseuds/agirlnamedtruth
Summary: Of all the days for Derek to surprise him with a romantic gesture, he had to pick the day he'd been forced to wear panties to school.





	

**Author's Note:**

> Written for the prompt "Any, any slash, crossdressing, you say you're gay, so why is there lipstick on your collar?" at [Rounds of Kink's Amnesty Round](http://rounds-of-kink.livejournal.com/). Fandom and pairing chosen by weekendgothgirl, so all the blame goes to her.

They’ve not been at this long but Derek can sense when Stiles is nervous. He won’t shut up for a start, telling him about every aspect of his day before Derek had leaned over and kissed him just to get him to be quiet for a blessed minute but even then, it didn’t work for long. He guessed it was his own fault, parking up by the school and picking Stiles up unexpectedly, saving him the drive home and the awkward climb out of his window at two in the morning to come and see him.

Derek pulled up to the house, giving up trying to calm Stiles. After all, shouldn’t he be the nervous one? He’d never done this for anyone before and he was certain of anyone, it wouldn’t be Stiles that got him to break his streak but here he was, leading the annoyingly adorable wretch up his front steps and into his wrecked home, a makeshift table put out for them and a crock pot bubbling away in the kitchen.

“Wait... is this a date?” Stiles asked, stunned into silence for the first time since he’d opened the car door.

Derek didn’t want to say yes but he didn’t want to say no either. Playing it safe, he shrugged and appraised the situation casually. “I cooked.”

“You’re not going to poison me, right?” Stiles joked, nudging him lightly enough that Derek only bristled, holding himself back from fighting back like his instinct begged him too. Playing rough with Stiles had been what had gotten him into this mess in the first place.

“I’m not going to poison you,” Derek confirmed before glancing at him. “Not today.”

“Good because I have to pass Friday’s history quiz...” Stiles started again, rambling on, the rest of his complaints about the test going over Derek’s head as he served up the world’s most basic chicken stew, hoping that Stiles might not be able to talk and eat at the same time. He was proved wrong. So wrong.

When the meal was finally over, Derek took the plates, almost running to the kitchen so he could breathe for a minute on his own. He really wasn’t used to this whole _being with people_ thing and Stiles was an overwhelming place to start. But as he laid the plates in the sink, he felt arms wrap around his waist, a warmth at his back that could only be Stiles snuggling in and he felt himself relax back into him. This was what he needed, peace and quiet and Stiles. Three mutually exclusive things, apparently.

“Thank you for dinner. I just usually get take out or you know, sometimes Mrs. McCall cooks and we have lasagna, she does a really good lasagna, have you had it? Probably not, you don’t really do dinner much, do you? Except now, obviously. You never did say if this was a date or-”

Derek turned, grabbing Stiles by the back of his neck and pushing him up against the opposing counter, keeping him pinned face down with his weight until the boy had gotten his breath back. “Why are you talking so much?”

Stiles laughed nervously, wriggling underneath him, trying to divert Derek’s attention. “You know me...”

“That’s right, I do know you,” Derek said as he nipped at the back of Stiles’ neck, sniffing around his hairline, trying to work out what it was that had him so nervous while knowing this wasn’t necessarily the healthiest way to work it out. “I know when something is wrong.”

“Nothing’s wrong, I just...” Stiles fell quiet, grinding back into Derek’s hips as his breath caught in his throat, Derek’s teeth worrying a particularly sensitive spot at the base of his throat. Only just remembering in time to reach up to his collar... a fraction too late.

Derek pulled back, confused and although he’d never let it show, a little bit hurt. “Why is there lipstick on the inside of your collar?”

“It is not what it looks like!” Stiles said, pulling the offending neckline away from his skin and glancing down at it, seeing how bad it looked. Pretty fricking bad.

“It looks like you have lipstick on your collar,” Derek stated, looking him up and down for any other telltale signs but other that the bright red smudge against the pale blue of his shirt, he was perfect. Or perfectly Stiles-like at least.

Derek stepped in close again, inhaling deeply even though he knew that if Stiles had smelt of anyone else, he would have known it the second he’d gotten in the car. But all he smelled of was soap. A lot of soap. Maybe he’d showered to get her scent off him. But fuck, he’d made it overwhelmingly clear that he was gay. Jumping into Derek’s lap every time he saw him like an enthusiastic but disobedient puppy had convinced Derek he was into him and only him, even though they’d never used the word _exclusive_.

Stiles sighed, knowing he wasn’t getting out of this one without either fucking up everything or telling the truth. And he really didn’t want to fuck this up. “What I mean is... that’s not the worst of it.”

Derek couldn’t stop his eyebrows shooting up at that thought, his mind racing to all the dark places he couldn’t stop it from going but he crossed his arms, waiting for the explanation of a lifetime. 

“I was playing truth or dare with the guys on the team, after winning the game last night and Scott asked me something I really couldn’t answer without giving us away so I had to take a really bad dare as a forfeit...” Stiles explained, pulling his shirt off and setting it on the side, showing him there was no lipstick anywhere else.

“You had to kiss someone for a dare?” Derek asked, his heart starting to slow and his blood cooling down. He could live with that. He didn’t want to think about it but he could live with it. 

“I wish...” Stiles said with a grin before quickly wiping it off again, just like he had earlier with the lipstick when he saw Derek’s car pull up. He reached for the zip on his jeans, biting his lip before taking the plunge and pushing them down dramatically. “I had to wear these to school. With Lydia’s lipstick.”

Derek had to bite the inside of his cheek to stop himself from saying something. Something about how it wasn’t funny or embarrassing or that he wasn’t going to take the piss out of him for eternity because the sight of him stuffed into hot pink lace French knickers was actually... hot. 

Holding his tongue on that thought, he dragged his eyes away from Stiles’ semi-hard dick peeking out of the gaps in the lace and returned his gaze to his eyes, putting on his best poker face. “That’s it?”

“That’s it?” Stiles mouth fell open and Derek had to look down again to stop himself thinking about how much he wanted to bite that pouting bottom lip. “Not only did I have to wear them all day at school which was fairly humiliating enough but I didn’t get a chance to go home and change them because you suddenly wanted to start acting all romantic and cook me dinner, that now I’ve ruined a perfectly good night of fantastic sex because I’m wearing girls’ underwear.”

“Whose is it?” Derek asked before he could stop himself, hiding behind a mask of indifferent curiosity.

“I don’t know, mine I guess? They were new, I promise,” Stiles clarified quickly before muttering. “It’s not like I have a collection lying around the house or anything.”

“Shame,” Derek said with a shrug, deciding he needed Stiles to stop talking again. “They suit you, turn around.”

Stiles blinked for a moment before shuffling back around with his jeans still around his ankles, his shoes stopping them from going any further. “They do?”

“Mmm,” Derek hummed in agreement with his earlier statement, appreciating the way the lace clung to his cheeks, riding up to sit between them. “Bend over.”

Stiles did as he was told, a shiver of anticipation climbing up his spine as he felt the stiff fabric of Derek’s jeans rub against his ass, the outline of his cock pressing into him, rock hard already even though they’d barely done anything. “It really turns you on, doesn’t it?”

Derek grinned but he kept his voice from giving it away. “Not another word or I’ll use them to gag you.”

Stiles opened his mouth to say something clever back but he closed it again, knowing Derek always kept a promise, even if most of his threats were empty. Instead he pushed back against him, swaying his hips to grind temptingly against Derek’s cock, begging to be fucked without saying a word.

“Not yet, princess,” Derek said with the edge of a growl, grabbing his hips and stilling them, moving down onto his knees. “Let me see you first.”

Stiles leaned forward, putting all his weight onto the counter as he reached back to spread his cheeks, trying to pull the lace out of the way but his nails got caught in it and it just stretched tighter. 

“Such a pretty pussy, it’s a shame you’ve kept it hidden away,” Derek said, his heart racing as he steered them into unchartered waters but Stiles groaned against the cold counter, clenching his ass for him encouragingly, the lace pulling tight over his cock as it got harder, pre-come staining it. “Let me see it properly, baby.”

Stiles adjusted his grip, putting all his weight on one shoulder as he wrenched the lace out of his ass, pulling it to one side so that his hole was finally bared, using all his strength to keep it hooked around his fingers.

“That’s better,” Derek cooed soothingly, leaning forward to press a kiss to the chaffed skin, smiling into it when Stiles moaned wantonly, pushing his ass back into Derek’s face. Derek pulled back, aiming a quick, sharp spank at the cheek still covered in lace. “If you want me to eat your pussy, you have to say please like a good girl.”

“Please, Derek,” Stiles said, his cock throbbing in the panties, begging for relief that he didn’t dare give it. They’d never played this game before but he was getting good at reading Derek, knowing when he wanted him to lie back and take it and when he wanted him to be mouthy so he’d have to be punished. Right now, all he knew was Derek had found something he _really_ liked and that alone turned Stiles on like mad, enough that his cock could wait, that was for sure.

“Say it,” Derek growled, biting the firm flesh of his ass. Not hard enough to draw blood or to turn him but enough to make him yelp in surprise, his dick giving another hopeful twitch.

“Please eat my pussy,” Stiles begged, spreading his ass cheeks further apart, his hole fluttering as he tensed, desperate for it, saying it out loud making him want it even more.

“Good girl,” Derek said rewardingly, helping Stiles step out of his jeans and shoes before raising his head and pressing kisses up the back of his thighs, teasing him, seducing him.

“Fuck, Derek, please...” Stiles begged again, with much more urgency, feeling like he would explode if he didn’t get some relief soon. This whole panty thing was clearly affecting him much more than he ever thought it would. Maybe he should have gone for the three pairs for $20 offer after all.

He gripped the counter hard as Derek’s mouth finally pressed against his hole, the tip of his tongue circling the tense muscle before he licked over it properly, working it like it was a clit before he finally pushed inside, slowly stretching him open with his tongue until he had him desperate again, needing more.

“Please fuck me,” Stiles said, reaching back to curl his fingers in Derek’s hair, getting his attention with a light tug. “Fuck my pussy.”

The words were out before Stiles had even thought about what he was saying but he didn’t regret them when Derek surged up, his hand reaching up to his hair, nails scratching down to the nape of his neck where it was too short to pull.

When he heard Derek’s zipper go down, he held his breath expecting him to thrust straight into him but instead he felt Derek’s fingers against his hole, cold with lube. He knew he should be grateful, he was still quite tight but he was impatient to be fucked, greedy for Derek’s cock. He counted as Derek put one, two then three fingers inside him, working through each step until he was gaping for him, pitifully clenching around his fingers to keep them inside each time Derek pulled back.

“Like that, baby?” Derek asked close to his ear, voice low but making sure he was heard over Stiles’ endless stream of requests for more. “Like knowing I have three fingers buried deep in your cunt?”

Stiles groaned louder, the word going straight to his gut, twisting something deep and primal inside. He could feel the heat rise in his cheeks as he nodded. “Yes but I’d rather have your cock.”

Derek growled low in agreement, the rustle of fabric barely preceding the feel of his fingers sliding out of his ass, guiding his cock in instead, only the slightest discomfort as he took him, already stretched wide from his fingers. As Derek bottomed out, filling him up, he finally sighed and fell quiet, satisfied for a moment as Derek thrust slowly in and out, getting him used to it, getting himself used to the feel of Stiles’ ass, hot and tight around his cock, the lace of the panties catching against his dick every time but it didn’t stop him. If anything it made him move faster, his hands curling around Stiles’ hips, toying with the waistband, focusing on how vivid the pink looked against Stiles’ pale skin, how Stiles’ knuckles were turning white from gripping onto the counter so hard and how good it felt to sink in and out of that pretty pert ass, framed by cheap, tight lace, threads pulled where Stiles had grabbed it too tight.

Reaching back, Stiles captured one of Derek’s hands, uncurling the possessive grip around his hip and laying it instead on his cock, the wet patch embarrassingly big now, the lace sticking to his skin even when he tried to pull it away, tried to push Derek’s hand underneath it. “Fuck, touch me, Derek...”

Batting Stiles’ hand away, he yanked the lace down until it sat under his balls, firmly taking his cock in his hand and stroking in time with his thrusts, the whining edge to Stiles’ moans telling him it wouldn’t take much to get him off. He was rewarded, and proved right, soon enough when Stiles cried out, clenching around his dick as he came over the counter top, fingers scrabbling at its surface, desperately trying to find something to cling onto as pleasure burned through him, his skin on fire with it until it flooded out again, leaving him spent.

When he could muster up the energy again, he reached back and clumsily swatted Derek’s hip, their code for Stiles tapping out, giving up his body for Derek to use however he needed to in order to get off, as hard and as rough as he liked. But not today. Instead Derek leaned down, scooping him up so he was in his arms, keeping his cock buried deep and his thrusts slow and intense. “Want me to come in that pretty pussy, baby?”

Stiles keened, nodding, eyes lidded where he still hadn’t properly recovered. He knew in this state he would likely agree to anything Derek wanted so he made the effort to look over his shoulder, backing up his wordless agreement with as much eye contact as his exhaustion could afford him. “Come in me, fill me up.”

He squeezed Derek’s hip encouragingly, clenching lightly around his cock, shivering as it sent an aftershock through him, trying to focus on Derek’s eyes still, kissing him as thoroughly as the awkward angle would allow. He didn’t let go of him until he heard him groan and felt him come in his ass, hot and wet, dripping out of him as Derek pulled out, making him feel deliciously dirty as Derek righted his panties, making sure the lace was bunched up again, stopping too much of his come from leaking out.

There was still the washing up to do but Derek ignored that, taking Stiles by the hand and leading him upstairs to bed. “Next time, keep the lipstick on. _Baby_.”

**Author's Note:**

> As of 01/01/18, I'm opting to disable comments. [More information here](http://archiveofourown.org/works/13077201).


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